Dimethyl Sulfoxide → HCID 10380396, Verbindung

A solution of 1.62 mL (22.73 mmol) of dimethylsulfoxide in 60 mL dry methylene chloride is cooled to -78° C. and 1.44 mL (16.53 mmol) oxalyl chloride is added dropwise. The mixture is stirred 0.5 hour at -78° C. and a solution of 1.0 g (3.31 mmol) of 1-(3-pyridyl)-4-hydroxy-8-(2-tetrahydropyranyloxy)octane in 15 mL dry methylene chloride is added and the mixture is stirred for 10 minutes at -78° C. The mixture is warmed to -60° C. and maintained for 15 minutes at that temperature. The reaction is quenched by the addition of 6.9 mL triethylamine. The cold bath is removed and the reaction allowed to warm to room temperature. The reaction mixture is extracted with 150 mL methylene chloride and washed with saturated sodium bicarbonate solution. The organic phase is dried, filtered, concentrated and chromatographed using 3:2 ethyl acetate, hexane to yield 1-(3-pyridyl)-4-oxo-8-(2-tetrahydropyranyloxy)octane; NMR (CDCl3): delta 2.6 (t,2H), 2.4 (t,4H).

1. stirringthe mixture is stirred for 10 minutes at -78° C
2. temperatureThe mixture is warmed to -60° C.
3. temperaturemaintained for 15 minutes at that temperature
4. customThe reaction is quenched by the addition of 6.9 mL triethylamine
5. customThe cold bath is removed
6. temperatureto warm to room temperature
7. extractionThe reaction mixture is extracted with 150 mL methylene chloride
8. washwashed with saturated sodium bicarbonate solution
9. customThe organic phase is dried
10. filtrationfiltered
11. concentrationconcentrated
12. customchromatographed

ORD-Eintrag

ord-0f4b4ab6881c4b0a9d7e56a9f964ce5c

Quelldatensatz

uspto-grants-1991_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05025025